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Gary Vaynerchuk
My father, if he put 200,000 and he would have $42 million. I got an allocation into Facebook. He said no, he had more money than me. It's 2011. I just built a massive business for him. If he put 200,000 and he would have $42 million, all of his no's of his life can't offset that. No. That is the cynicism tax. This is the GaryVee audio experience.
Interviewer Matthew
The cynicism tax. Why being realistic isn't as real as real as you think. So stop mistaking negativity for reality and start using optimism to get things done. And I just wanted to get your definition of what a cynicism tax is.
Gary Vaynerchuk
A cynicism tax is defined in my mind of you're deploying a perspective of no without putting in the efforts to see if it's a maybe, thus rendering you having no capacity to ever find upside that others don't see or even few see or the masses don't see. When you're in a practical optimism framework, you're saying maybe to everything. And when you say maybe to everything and you have the humility to quote, unquote, waste your time, AKA use your time to potentially say yes to something that most will say no to. How do you think I found myself being right about email marketing? About having a website around? Google AdWords, Influencer Marketing, Mobile? Like everything that I've watched, anyone who's innovated is met with no's. I am in practical optimism, which. Oh, by the way, let me address this. Cause I saw a piece of content this weekend where it said that I'm the king of toxic positivity. And I was laughing with how many people? And you know this, a lot of people are trying to weaponize this term, right? Nothing could be more interesting to me than people have decided to create a term called toxic positivity and and try to weaponize it against humans. It's truly one of the saddest things I've seen in the world. Here's why. Toxic positivity is really just slang term for delusion, right? Or a dream, right? If that word didn't exist, they'd be like, Gary's just selling them a fake dream, right? For me, all I talk about is practical truths. All I believe in is accountability. The market is always right. People are confusing practical optimism with toxic positivity or delusion because they don't know the difference between trying for a little while or wasting all your time and money on it forever. I am the king of what Some people would say wasting minutes and hours and days on hypotheses that end up not being true. But that level of curiosity and practical optimism has also led me to 40 things that are so true that the upside of those 40 truths has created remarkable economic and emotional happiness. The tax on cynicism is none of the people that deploy it. Sammy. Could have ever discovered the gold at the other side of the rainbow. Cause they never slid down the rainbow. I hope you're enjoying the podcast right now. Make sure you follow the podcast. That's why I'm interrupting. Let's keep going on this show, but follow the podcast. It'll make my mom super happy.
Interviewer Matthew
Cause they never. They don't even try. Cause they're not even. They're not even in the game.
Gary Vaynerchuk
And like real talk, if you are trying to accomplish something, but you've already talked yourself out of it and you're not doing it, doesn't that actually render it 100% impossible? The end.
Interviewer Matthew
You miss 100% of the shots you don't take. Or what was I quote?
Gary Vaynerchuk
And people are so scared and are so believing the negativity in the world that they choose to weaponize cynicism as a protection mechanism. And then if that's not enough, they go and try to deploy toxic positivity on people that are practically optimistic. I cannot laugh more about that. I also think it's really.
Interviewer Matthew
I also think people are fearful based.
Gary Vaynerchuk
Yes, that's exactly what's happening. They're so feared that they're in misery, loves company, and they try to deploy cynicism and labels to make sure everyone else doesn't do anything either.
Interviewer Matthew
What about when it's like, sometimes, like, your family, like, my family are immigrants. Right? And it's all, like, protection because it's like, I love you so much that I don't want you. Like, we need to be, like, protected from these risks. We did all these risks.
Gary Vaynerchuk
I agree.
Interviewer Matthew
Now, like, protect yourself.
Gary Vaynerchuk
Makes sense. How old are you?
Interviewer Matthew
I'm 31.
Gary Vaynerchuk
Great. Tell your parents you're 31. Like, when people ask me, like, what do I do, Gary, with that? I'm like, you know, like, I get it. Like, I didn't ride a bike. I'm scared of dogs as a kid, and I was scared of swimming because my mom was scared I was gonna get drowned and bit by a dog. I know what fear is. I have no judgment. Unlike, you know, it's funny. Unlike people that are affected by my optimism and want to sling toxic positivity, I don't Call it toxic cynicism. I don't call it toxic fear. Notice what I called it. The cynicism tax. I don't even wanna. I always laugh when people wanna hurt. I don't wanna. I don't even wanna use that word, toxic. Cause I don't wanna hurt people's feelings. But do I believe that most of the people that read this article or watch this clip have a cynicism tax? Yes, I do. I think most people do not achieve. Now, to the. Let me counter myself. Let me join the ranks. Do I think that there are people that are downright delusional? Like, delusional? Sure. I meet them all the time. You know, those people do gravitate to me. You know, it's funny. I get both sides. You know what gravitates to me? The extreme cynics that are, like, so tired and are 10 years into their cynicism that they're actually ready for my practical optimism. They're not in year one where they're gonna leave a comment. King of toxic positivity. They're in year seven where they're like, clearly, my way didn't work. I wanna actually know what this guy's been talking about for the last 20 years. And then there's people that a lot of those people are making fun of and think exist, which is like, delusional people. Which is why Sammy. Matt, I always talk about work ethic, accountability. The market is the market. Yes, you should quit after four and a half years of sucking at the same thing over and over. Like. Like, you know, like, it's almost like,
Interviewer Matthew
for the delusional, but it's almost like the reps are the proof. Right. Of, like, that thing that you're striving for.
Gary Vaynerchuk
It's sports.
Interviewer Matthew
Like, you're saying you put in that work. That work ethic is the proof.
Gary Vaynerchuk
It's sports of that.
Interviewer Matthew
Yeah.
Gary Vaynerchuk
I laugh when people want to take shots. I'm like, have you looked at my baseball card? Turn it to the back. Do you understand what I've done? It's your world. I'm here with Steve from Vayner speakers. I told Steve and Zach, like, as early as I met them. When I met Steve, I was already somewhere. Zach got me a little bit earlier. But you actually. Actually, that's right. Steve. Like, right. Steve knew of me and I told everybody I was gonna be a very successful speaker. Whether I was brash and delusional or positive. If I was deploying toxic positivity on myself or. Or not. Or Steve was like, or Zach thought little too brash or too much cursing or not professional enough or. Yeah, I just don't get it. Which is super valid. I've been wrong about people all the time. It didn't really matter in 2011 what I thought or what they thought. It just plays out. It just plays out. And so I would just tell everybody who's reading this that if you're willing to be quiet and really understand, are you on the side of paying a cynicism tax? If you're on the side of the other side of the pillow delusion at scale, try to find this middle, which is grounded in maybe I'm a maybe trying to find yes guy. I'm not yes at everything, but fuck, man. Boy, do I see the world loaded with people that are no one. I mean, my father literally says no to everything. I'm gay.
Interviewer Matthew
Sorry. I liked that because that was a bar. I was like, let him cook. I was like, yeah, I can go ahead.
Gary Vaynerchuk
You know, that's it. How could you possibly achieve something if you killed it before you started? And then that's what got me down. Now I'll give you the insight of my career. That's what then got me to. Why are people doing this? Oh, wait. People are saying no to protect themselves from losing publicly. Think about how safe it is. I'm gonna shit on people like Gary and others who are positive and say they're toxic. Positivity. That makes me feel like I'm doing something. Cause in real life, I'm doing nothing.
Interviewer Matthew
And now the comment section too. It's so easy to be able to do that. You feel like you're.
Gary Vaynerchuk
And you feel like you did something like, yay, I got 150, like, on this post that I'm like, talking about this weekend. Ooh, 900 people agreed with me. See, Gary, you're wrong. I'm like, okay, see on the other side. Can't wait. Let's see how this plays out. There's really no logic, like, no actual practical logic to be a queen of cynicism. Optimism is not the same word as delusion. And cynicism is not the same word as thoughtful. It's good to be thoughtful so you don't buy a million dollar lottery ticket like you don't want to be. Right. But again, I think people think cynicism is the same as, like, well, Gary, if I wasn't cynical, I would have invested in that beachfront property in Peru with my neighbors, and we all lost our money. Like, that's not cynicism. That's being thoughtful. Cynicism is deep. What's the definition? What's the Webster's definition of cynicism?
Interviewer Matthew
Team an inclination to believe that people are motivated purely by self interest, skepticism.
Gary Vaynerchuk
That would be like the people selling us the beachfront property in Peru aren't just selling a beachfront property and letting us make a decision. They're trying to trick us to take our money and it's gonna be bad for us. That's different than this is a neutral business deal. And should we, the four of us, you know, should we all pile in our dollars? We got a new friend here. Can you add 20 bucks to it and can he. Can we buy this property? The cynics will point to the nine times it doesn't work out. I'll speak to the time where I bought beachfront Malibu property for 100,000. It's worth 40 million. I didn't do that. I'm just saying good examples. But like for. But for example, everyone, I mean, I've got a real one. When I put all my money in, my. My father, he's gonna hate this. I'm not sure we should use this, but I just want you to hear it. My father, I got an allocation into Facebook the same time I did. He said no. He had more money than me. He said, It's 2011. I just built a massive business for him. This is not 1994. If he put 200,000 and he would have $42 million. All of his no's in his life can't offset that no of his life. That is the cynicism tax.
Interviewer Matthew
It's also strategy of like, are you using the strategy of cynicism or the strategy of optimism?
Gary Vaynerchuk
Right. And understanding that we are not talking about thoughtfulness and delusion, it's very important you weave that in. Like, I want to make a very strong point. There's a reason cynicism exists as a word and there's a reason why thoughtful or whatever. What's the opposite of cynicism? I use thoughtful first of mine. But there's other good words. I'm sure. Let's ask.
Interviewer Matthew
I think optimism is kind of it. Yeah.
Gary Vaynerchuk
Yeah. So these are the cousins, right? So right. To me, I use optimism, but that's not delusion. In fact, actually in ChatGPT, what's the difference between optimism and delusion is good. What's the difference between cynicism and thoughtfulness? I think are like really good prompts. Like, that's my point. The general public, when they hear cynicism and Optimism or positivity. I mean, the concept that there is even an ability to be toxically positive is so stupid. It's a misunderstanding of positive. What they're trying to say is delusion. It's sad that we're. We should kill that word. It's going to ruin the world. Stop saying toxic positivity. Start saying delusional. Because positivity and delusion are not the same. But you're tricking the kids. I'm fucking pissed about this. I've decided I'm pissed about this. You're fucking ruining an entire generation's opportunity because of your own hurt and loserness. Fuck that shit. Not letting that happen.
Interviewer Matthew
Putting it on T shirt, doing it. I think that's good. That's perfect for this article. And then we'll have it all finished up. Matthew, do you have them?
Interviewer Steve
When does. When you run into somebody who's in a no mindset, a. A scarcity mindset, what are like the first tactical steps you take to getting them to skew toward.
Gary Vaynerchuk
Toward at least maybe by actually saying yes to something they want to say no to, to see how not bad it is and to tell them that this will likely not work out. But this is just practice. Most people need to know what it feels like to lose $15,000 when they can't fully. They can afford it. Like they're not dead, but it's a fucking ding. Because once, if you really believed it, you're going to feel better than you think. That's the part that most people don't understand that if you actually believed it. Here's the. Let me break down the scenario. If you want to use example. You believe it's a good investment to put $15,000 into a group fund with 10 other buddies to buy a single family home for 150,000 and make money off the derivative. You believe it, you say no. They go on and do it. And by fucking year three, they're already paid back and making money for the rest of their life. You're fucking dead inside because you believed. Yes. But you allowed cynicism and fear to make you go, no, you go and put that 15,000 and it does not work out. You don't feel as bad as the first example. That is what I have to teach people to go through. Got it? How do you do it? It's different. It's just like working out. How do you get someone to work out? You physically drag the fucking ass out of their bed and bring them downstairs and go to the gym. Like until they do it you can't do it and they'll fight you tooth and nail. It's like an alcoholic.
Interviewer Matthew
I just wanted to kind of follow up on that because the things that I'm getting is like, it's either the worst feeling is like the regret of of not doing it, or like the worst feeling is the fear. Before you even start, like which one
Gary Vaynerchuk
do you think the worst feeling is? You fully believe something and you go against your feelings because you let fear stop you. But in your true heart, in like real talk, have you not done something in your life that you knew, you wish you did, you wanted to, but fear stopped you. And then it played out in a way that was good and you wish you were associated with that good. Do you know what that feels like? It feels the worst. Like you wish you dated that boy and said yes. You wish you bought that thing. You wish you invested in that stock, you wish you took that job. Like it's the worst feeling. The worst feeling is your soul is telling you yes. And your brain fear when you let that overpower your gut. Yes, you let your brain fear and then it like, let me give you so it works out, you're upset. Let me give you the reverse. Your brain fear says don't do it. Your heart and soul says do it. You take your brain and then thing does not work out. It doesn't feel as good as you think it does. The highs are much bigger on success than the lows feel in not success. And the highs are much higher than the good feeling of your no worked out. You're like, okay, like some people get off on it. See, told you. You nine friends are suckers. Like you get your high on that. But there's no, you didn't win. This is what I keep telling people, you didn't win. Like think about, is that what you want your life to be? That you make fun of your nine friends who took a chance? Like, is that fulfilling? So like again, like what? Like this is real talk, this makes sense. Like, is that what you want your life to be? Like your nine buddies failed, their restaurant investment failed. And what, you just be like, haha, I was the only smart. Like, what are you doing? Like, what is that life I'd rather lose with my buddies? Like the drinking nights of like making fun of us? Like, remember when we tried to buy a Chinese restaurant in Alabama? Like that 15 times you have that story over beers is worth the $15,000 that I like, you know, and again, everything's relative and money's important. Like I'M not saying that. I'm saying soul, your soul. I'm saying like, I mean, you can
Interviewer Matthew
get at the end of the road and then you're gonna look back and you're gonna see everything. Regrets you're not there with like your buddies anymore.
Gary Vaynerchuk
People have become, people have become intoxicated with like labeling everyone else without realizing it has nothing to do with their life. When the fuck did we all decide that we were God? People are literally walking around earth like they think their fucking opinions are the fucking end all be all and they need to fucking spread it near and wide on everyone's comment. Now I put out a lot of content, but I'm passionate about perspectives, but I'm not trying to impose my will on people. Like, I'm not going around the Internet and being like, you're wrong, you're wrong, you're wrong, you're wrong, you're wrong, you're wrong. I'm just putting out what I believe and like let the chips fall. That's very, very, very different. I'm out here doing things and letting the chips fall and living life. Other people are going around and just shitting on things. Cynical armies. And they think they're doing something. They're not doing anything. They're reacting to other people's doing and they think the shitting on it is their contribution. They're doing nothing and they're going to wake up soon and be like 50, 60, 70, 80, 90 and be like, oh wow, I did nothing. I've watched this happen. Pre social media. I had a family of two very opposites. People are about to get to 70, 80 year olds and realize they did nothing in their life besides shit on other people's dreams. That's great. Congrats. Hope you enjoyed that run on your only time on earth. What a fucking pathetic point of view.
Interviewer Matthew
You said that this is before social media. Cause I'm wondering too, like even on TV shows now I feel like TV shows, there's team this one or team this one. And the comment section is so opinionated that it informs even the show. And do you think you said it's pre social media because I was gonna ask, do you think it is social media that we all have an ability to leave a comment?
Gary Vaynerchuk
We all had our opinions. They used to just sit in the kitchen table. All of our great grandmas had all sorts of opinions. They were just confined to the park and their other two lady friends, the dinner table, right, the pta. Now we're contributing to the ether, but I don't people understand, like, here's one thing that I'm fascinated by. The cynics. They're accomplishing absolutely nothing.
Interviewer Matthew
What do you think makes them think? Because clearly, like, it's still feeding it, so they're still doing it at the cycle. Well, something must be feeding that validation that they're getting, right?
Gary Vaynerchuk
Yeah, they think they're doing something. They're confused. You know, houses are confused. An alcoholic, a drug addict, a narcissist. I have really bad news for people. If you spend your life going around and shitting on people around the Internet, you have a disease. It's called insecurity. Like, it's like, it's going to be widely understood as a massive disease. People spend five, six hours a night going around the Internet and shitting on people. That's a very hurt person. We didn't know alcoholism was a problem. You know that, right? Like, we knew, but like, we didn't know. Do you know what I mean? Like, we're like, oh, he's a drunk. You know, like, we do not understand this. And I am going to yell at the top of my lungs about this. This will be diagnosed in due time. It's a really bad thing. And cancel culture, like tearing down the establishment because of your own pain became. It's just. It just does not work. It has never worked. It just leads to a very dark and angry place because you're just in a cocoon of dark, toxic posit. Do you know, insane toxic positivity is. As if positivity is like a problem. It's one thing if you don't try and you shut your fucking mouth and you talk to no one and you're not trying by yourself, within yourself, right? Like, you're just sitting at home, you're not trying and you're not bothering anyone. I kind of am. Like, you know, my heart pours for that person. I'm like, yo, I hope I can find them and be like, you should try. It's a whole nother thing to not try and spend all your time, what you should be doing and trying to tear down everyone else who's trying. That's called cancel culture. That's called comment. Keyboard warriors. That's called a bunch of punk ass bitches.
Interviewer Matthew
That's a disease, right?
Gary Vaynerchuk
That's a disease.
Interviewer Steve
When you're interviewing, say, an executive, is this something that you can sort of spot in someone?
Gary Vaynerchuk
Yeah, sometimes. Only if, by the way, only in the extremes. In interviewing. Only the extremes. I knew in five seconds that Claude was awesome. Only if you're like in the top 10% to the extremes, like all of you. I couldn't really. I'm just like, you have to be like, top 10, like, delusionally, like, like almost like a Buddha. Like me. I think, like, a lot of people can read me early, even before I was me. Like, you just kind of know when you meet people, like, oh, wow, that's like a lot of positive energy. And then you watch quickly and think back it up, right? Brandon. I knew that about Brandon in five seconds. That's why I still know him 40 years later. First day of high school, I knew, knew. And then I went to a baseball card show with him six weeks in. And he worked hard. And I literally told my father, I'm going to hire this guy for the store in October of my freshman year of high school. Didn't work for us for eight years. From that, like, knew that all the way to the other side. There have definitely been people I've known. Like, I sometimes get like, visceral, human, like, goosebumps, like, turn in my stomach when someone's very negative. Like an animal, you know, like animals, like, run away. Like, I run away from people. It's been a great gift of my life. Run away. Where I've gotten caught is sometimes I know someone's hurt and I see them as a charity project. I've hired a lot of those. That's where I've hired poorly. They're not complete visceral poison. They're a charity project for me. And I blended my charitable work in my professional job and I want to stop doing that. And I've stopped doing that. Like, good news, all four of you are fairly new. None of you were hired as a charity case. Whereas, like, no bullshit, somebody could have gotten your jobs that was half as good as you, in my subjective opinion. Interviewing Because I wasn't able to detach my charitable energy from my operational energy, especially when it tends to always map similar to my dad, like, deeply insecure, which is always the tell. Usually older, you know, like some of the characters that are still around, like, fit that I just haven't fully reconciled yet, but I'm not adding anymore.
Interviewer Steve
How much of your success, very generally speaking, doesn't have to be anything specific, just generally. Do you think has to do with
Gary Vaynerchuk
this conversation skew toward.
Interviewer Steve
Toward maybe towards some of that optimism, allowing serendipity to sort of just play
Gary Vaynerchuk
out way more than you could ever imagine. Way more. Like if I had to put a percentage on it, a number that would make your head spin. There is a potential. My practical optimism framework. The fact that I approach almost everything with a maybe, with an effort to get to yes, has a substantial double figure. 20%, 30%, maybe more. Maybe I can't even see it. That's how much I know how big it is. Maybe all of it. It's really a big deal. That's why I'm passionate about it. Everybody, if you enjoyed this podcast, please go back and look at the prior episodes. They're loaded. I appreciate your attention and thanks for being part of this journey. See you later.
Date: March 19, 2026
Host: Gary Vaynerchuk
Guests/Interviewer: Matthew, Steve
In this lively episode, Gary Vaynerchuk dives deep into the concept of the "cynicism tax"—a hidden cost people pay for defaulting to skepticism and negativity rather than practical optimism. Drawing on personal experience and candid discussion, Gary and his co-hosts challenge the widespread confusion between thoughtful skepticism, cynicism, optimism, and delusion. Notably, Gary takes aim at the "toxic positivity" label, passionately defending practical optimism as a key ingredient to success, serendipity, and fulfillment in life and business.
Definition:
Gary defines the cynicism tax as the cost of saying "no" by default—refusing to pursue possibilities without giving them a fair chance. Doing so ensures you miss out on outsized opportunities that open-minded, practically optimistic people can access.
Personal Example:
Gary shares a story about his father refusing a Facebook investment. Had he invested $200,000, it could have turned into $42 million. That singular “no” overshadowed years of saying no to smaller things—a quintessential cynicism tax moment.
Protection as Cynicism:
Many people inherit cynical mindsets from families acting out of love and fear, aiming to protect them from risk. Gary empathizes, acknowledging his own upbringing filled with caution—but underscores that adulthood means taking responsibility beyond that inherited fear.
The Middle Path:
Gary stresses the need for balance: not pure naivety, not relentless negativity, but a blend of thoughtful optimism. He urges listeners to self-assess—are they defaulting to "no," or are they open to "maybe"?
Misunderstood Terms:
Gary rebukes those who weaponize the term "toxic positivity," arguing most "toxic positivity" is mistaken for delusion. For Gary, practical optimism always includes accountability and market reality checks.
Toxicity in Language:
He’s adamant about not labeling others as "toxic cynics," rejecting any rhetoric meant to hurt people. Instead, he analytically discusses causes and costs of cynicism.
Social Media's Role:
Amplified by comment sections and digital culture, cynicism proliferates because it's easier to tear others down than take action or try something new.
Validation Through Negativity:
Online cynics believe their negative comments are meaningful contributions, confusing reaction for action.
Regret vs. Failure:
The worst pain isn't failing—it's never trying when you believed you should have:
Allowing Serendipity:
Gary credits a significant chunk of his success to this optimism-maybe-mindset, which opens doors that cynicism slams shut.
Tactical Steps for the Cynical:
Push someone to say "yes" to something small they instinctively want to refuse, so they experience it not being catastrophic. The pain of regret usually dwarfs the pain of a manageable loss.
"All of his no's in his life can't offset that 'no' of his life. That is the cynicism tax."
— Gary (00:17; 11:54)
(On the cost of defaulting to ‘no’ – a missed Facebook fortune)
"People are confusing practical optimism with toxic positivity or delusion because they don't know the difference between trying for a little while and wasting all your time and money on it forever."
— Gary (01:38)
"It's sports. You put in that work. That work ethic is the proof."
— Gary (07:24)
(On consistency and proof, not just belief)
"Regret of not doing it is worse than the fear before you even start." — Interviewer Matthew (16:03 paraphrase)
"The worst feeling is your soul is telling you yes and your brain fear… you let that overpower your gut."
— Gary (16:15)
"Optimism is not the same word as delusion. And cynicism is not the same word as thoughtful."
— Gary (09:58)
"If you spend your life going around and shitting on people around the Internet, you have a disease. It's called insecurity."
— Gary (21:31)
Gary Vee reaffirms practical optimism—rooted in effort, accountability, and openness to upside—as a major differentiator for personal and professional success. The habit of cynical reflexes closes doors before they can even be tried, while a thoughtful willingness to say "maybe" and act on your beliefs—even at the risk of failure—brings growth, serendipity, and a richer story to life.
He implores listeners: examine where cynicism or fear is costing you opportunity, and trade default skepticism for practical action, curiosity, and grounded optimism. The regret of missed chances far outweighs the bruise of a manageable loss.
Listen to the full episode for Gary’s signature energy, more stories, and actionable advice.